First Time
by the immortal fish
Summary: A fluffy one-shot concerning Sam and Dean's loss of virginity in high school.


Sam Winchester lost his virginity on a Saturday night.

It was April, and warmer than it should have been. Light from the setting sun streamed through Sam's bedroom window on the day that he gave his heart and his purity to Emma Sorenson. She was a sandy-haired, bespectacled mathlete, a girl who organized the dresses in her closet by color and the history notes in her three-ring binder by death toll. She knew the stories of all the constellations in the sky and her favorite book was Anne of Green Gables. She wrote Sam love letters, short and long, and sticky notes and lined paper, notes that she slipped into his textbooks and locker and backpack. Other girls at school didn't pay her much attention. They thought of her as a plain, even boring girl. Sam Winchester had never seen anything more beautiful.

Dean Winchester lost his virginity on a Friday night… Or was it a Saturday morning?

Either way, he was drunk, and it was the time of his life. The party was in celebration of the end of his sophomore year, but there were more than just sophomores there. There were always more people than one would expect at Braden Harper's parties. Dean attributed this to one fact and one fact only – Braden always managed to get more than enough alcohol. And alcohol was always the key to a fucking awesome party. Dean had found himself playing truth or dare with a group of juniors. His senses numbed by the alcohol, he didn't give it a second thought when he was dared to fuck Ashley Hart. She was bleach-blonde and stunning with huge boobs and legs for days. He didn't feel much guilt when she pushed him to the floor of the trailer parked outside of Braden's house and shoved her hand down his pants.

Sam Winchester lost his virginity in silence.

He hadn't expected it to be loud, like in porn. He liked it better calm. They didn't need to communicate with words. Every touch was a word, every kiss a story. When Sam ran his hand through Emma's hair, it meant, "I love you". When she kissed his neck in return, it meant, "I love you too". Every breath was orchestral, every kiss melodic. Every touch was a love letter, a thousand words in a thousand languages, all of which screamed proclamations of love, the kind that echo through empty mountains and carry through busy streets in big cities. Somehow, they were exponentially more meaningful than the sticky notes Emma slipped into his biology textbook. Sam knew the relationship couldn't last, so he made sure right then and there that she knew how he felt, and she did the same. It wasn't a beach at sunset or a drive-in under the stars, but it was just as romantic.

Dean Winchester lost his virginity in a much louder fashion.

Admittedly, her outbursts of dirty talk were somewhat annoying and yes, he was disappointed when she took off her bra, but that didn't matter because he had just gotten a blowjob, and _damn_, that was good. Dean learned very quickly that she had had a lot more experience than him. She knew how to use her tongue to her advantage. She knew used her fingers systematically, like a concert pianist on a grand piano. She even kept a handful of condoms in her purse. (Dean had to admire the preparedness of this girl.) He didn't mention that he was a virgin. She didn't ask.

Sam Winchester lost his virginity in the romantic way.

Even after it was over, Sam still held her close. He watched the rise and fall of her chest in awe, counting her breaths as she fell asleep. He kissed her freckles and stroked her hair. The next morning, he rose early and made eggs, toast, and orange juice. He left out the bacon – Emma was a vegetarian. He brought it to her on a platter right before she woke up. There were a million adjectives that could have described how great Sam felt watching the light fill her eyes as she woke up, but all his brain could put together was that he was more than grateful that dad and Dean were decapitating werewolves in Kentucky that weekend.

Dean Winchester never spoke to Ashley Hart again. He wasn't even quite sure what to do when she tossed him her bra and winked before getting into the cab she called to take her home. This situation was remedied the day after when Dean found that chucking women's undergarments at little Sammy garnered a generally negative response from the twelve-year-old.

Sam Winchester broke up with Emma Sorenson on a bench outside the supermarket that summer. He was going to Stanford, after all, and she was studying English at Kenyon College in Ohio. Both agreed that they had a good relationship but it was time to move on.

Sam Winchester sought fulfillment from his first time, and fulfillment he got.

Dean Winchester sought to get laid, and the bragging rights, he concluded, were almost as good as the sex.

**Author's Note: **Hey, if you guys like it, I would be hugely appreciative if you would drop me a review. :)


End file.
